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Since Artsy's primary Skills don't rely upon each other (such as Cooking, Fishing, and Gardening), you can pick and choose which primary Skill to focus on. However, since her career and primary source of steady income is Music, I recommend focusing on Guitar skill first, then Painting, and lastly, Writing.
Guitar
Purchase a Guitar in the hobbies and skills category of the Buy mode's study tab, and put it in your Sim's Inventory so you'll have it at all times.
"Meet Band Members" and "Chill with Band Members" during your first Career week.
"Study Music Theory" most days at work until your Guitar skill reaches level 10.
Once you have achieved Guitar skill level 5, start Playing for Tips on your days off in town until you've earned $25,000 to achieve Money Maker Skill challenge.
Starting at Guitar skill level 5, purchase sheet music at the local Bookstore and learn a new song at each and every skill level until you've reach skill level 10 to achieve Master Guitarist Skill challenge.
Starting at Music career level 6 (Lyricist), start getting to work an hour or two early and select "Performances".
Play Guitar at every party fundraiser party The Diplomat Sim throws to achieve Guitar Star Skill challenge.
When you've reached level 8 of your Music career (Lead Guitarist), you'll only be working 3 days a week. Take advantage of your 4 days off to max your Guitar skill and start focusing on your PaintingSkill.
Painting
Purchase an easel in the hobbies and skills category of the Buy mode's study tab, and place it in the most decorated room in your Sims' house.
Paint 30 small paintings in your spare to raise your Painting skill and achieve Brushmaster Skill challenge.
After achieving Brushmaster Skill challenge, start painting large paintings to achieve both Proficient and Master Painter Skill challenges.
Writing
Purchase an inexpensive Computer, and place it in the most decorated room in your Sims' house. Eventually, you'll want to replace it with the best computer possible.
I never recommend ever choosing "Refine writing skills", and write books and novels instead (please see Books and Novels Table below), and should be enough to fulfill most or all Skill challenges and Opportunities...